What: The Standard hotel’s ice-skating rink has returned for its second season, bolstered by an entertainment lineup that makes a case for its identity as the low-key third arm of the bôites thumping up above (Johnny Weir recently performed to a mash-up of Glee’s “Rumour Has It” by Adele, and an ongoing hockey tournament keeps spectators rooting on the weekends). Nights when flamboyant hip-shaking figure skaters are not performing are ideal for more romantic sliding under the lights. For those who aren’t sure of foot, lessons are available—as are spiked hot drinks at the rinkside Kaffeeklatsch pop-up. White, dark, or peppermint hot chocolate as well as soups, waffles, and sweet and savory crepes are just a few of the selections to share.

Where: The Standard, New York, 848 Washington Street, Meatpacking District

What: A marriage of New York’s most revered concert hall with one of the most acclaimed hip-hop artist to emerge from its boroughs is a love story in itself. But when Jay-Z takes the stage at Carnegie Hall for two nights in February, the evening will also have an epic resonance. Proceeds will benefit United Way of New York City and the Shawn Carter Foundation—a gesture that won’t be lost on the object of your affection. If snagging a pair of the much sought-after tickets proves elusive, you might instead opt for a performance a few blocks to the west—The Kills arrive at Terminal 5 in New York on February 11, and tickets can still be tracked down online.

What: When it first premiered in 1981, Stephen Sondheim’s musical Merrily We Roll Along, based on the 1934 play of the same name, was coolly received—the themes in the story that followed a Broadway composer turned film producer and the decades-long vicissitudes of his friends and paramours were considered a tad dreary for musical fare (indeed, they still aren’t for the faint of heart). After several revisions of the production, however, audiences found themselves wooed, and the production went on to win the Laurence Olivier Award for Best Musical in 2001. To do some wooing of your own, suggest a night out at the New York City Center, where the “Encores” series puts on Merrily for a two-week-only run, with a cast that includes Colin Donnell, Lin-Manuel Miranda, and Celia Keenan-Bolger.

What: It’s said that the way to the heart is through the stomach, and the quickest route to take in Manhattan may be Haven’s Kitchen—the newly minted food community with cooking classes, lectures, a market, and a supper club. Located in a charming carriage house several blocks from Union Square, the farm-to-table school aims to give guests the tools to cook with a deeper awareness of what they’re eating and where it came from (the staff shops primarily from the Union Square greenmarket). February’s class offerings are as mouth-watering as they are exquisite—Valentine’s Cookies, Sparklers and Caviar, Wines that Woo—and, for the more laid-back affair—Tequila and Fish Tacos.

What: A love triangle of extreme stakes unfolds in François Truffaut’s The Last Metro, starring Catherine Deneuve (someone who knows a thing or two about seduction), who is being honored with the Film Society of Lincoln Center’s Chaplin Award this spring. If your date appreciates suspense, clandestine affairs, and good hair, slip in to the screening and swoon along with Deneuve and Gérard Depardieu as they engage in I-love-you-I-love-you-not back and forth. Afterward, sit down for wine and cheese at Jason Denton’s Indie Food and Wine.

What: A date at the former incarnation of the Beatrice Inn used to mean lively jostling on the dance floor until the early hours, with anyone who was anyone who was anyone wearing a fedora. In its new incarnation as a restaurant—set to open at the end of the month—the establishment adopts a quieter, more romantic approach. “Warm amber light from the two fireplaces, low ceilings, and cozy seating will create dramatic glow for those looking to escape the everyday chorus,” says owner Emil Varda. The new chophouse features two dining rooms and a bar; signature dishes include Wagyu steak with Bordelaise sauce, as well as a plethora of vegetarian options.

What: There’s lots of imagining to be done at the Brooklyn Museum’s upcoming exhibition “Playing House,” in which you and a companion can wander through eight period rooms that have been transformed by the installations from artists Betty Woodman, Anne Chu, Anne Agee, and Mary Lucier. The artworks, designed to bridge the past with the present, spring from every nook and cranny—magical birds poking their noses through doorways, fabric flowers springing from a centerpiece, a hand-drawn wallpaper that transforms a parlor into a fictional manufacturing company. This is a domesticity that’s easy to try out for an afternoon—with no strings attached.

What: With last year’s wedding of Prince Albert to Charlene Wittstock, the world was reminded of Monaco’s storied romantic past and now, the romance comes Stateside with Les Ballets de Monte Carlo’s Joyce Theater debut. Known for their emotive movement, the performances are also an ode to the beauty of artistic matchmaking. Choreographer Jean-Christophe Maillot’s featured works are embellished by experts of other mediums; in the New York premiere of Opus 40, backdrops and costumes are designed by George Condo, and Part I from Altro Canto is set to the music of Monteverdi, with costumes by Karl Lagerfeld.

What: Stroll through the Luxembourg Gardens, peruse store windows and street fairs, wonder at the fifth arrondissement, all from the halls of MoMA when “Documents Pour Artistes” by photographer Eugène Atget goes on view this month. Skilled in his own right, Atget’s masterful repute came almost by accident—his main objective was to create images as inspiration for other artists. Hopefully, his visions will also inspire your next outing together, perhaps to the City of Light itself.

What: At last, the genius behind City Bakery’s iconic salads has opened up a bar of her own. 606 R&D, the Brooklyn brainchild of Ilene Rosen, formerly the savory chef at City Bakery, and Sara Dima (a former manager there) brings delicately minimal and deeply comforting plates—cake doughnuts and Mortadella roll-ups with cream cheese, for example—to Prospect Heights’ food frontier. Cozy up to their casually chic bar with your date and a S&S #1, the bittersweet drink du saison. For a Manhattan escape, head to David Chang’s Booker and Dax, a new high-tech drinking den nestled into the wildly popular Momofuku Ssäm Bar, where the cocktails distinctly imply: “Don’t try this at home.”

Where: 606 Vanderbilt Avenue in Prospect Heights, Brooklyn

When: Open for dinner, drinks, and market goods; breakfast, brunch and lunch soon to come.

It’s not without coincidence that the northeast’s chilliest month (historically, at least) is also known as its most affectionate. Against the backdrop of a bone-chilling February, even small gestures—a cup of hot chocolate, a musical note struck clean and pure—can cultivate a deep and beguiling warmth. Here are ten ideas for enchanting winter dates, for Valentine’s Day and beyond.